In Luke 16:1–9, Jesus told his disciples an odd parable where he used a dishonest manager as an example of shrewdness. What did he mean? Imagine a discussion about this between disciples Simon (the Zealot) and Matthew.

________

“Matthew, you know more about these things than I do. Why did the Master commend the dishonest manager’s shrewdness?”

Simon’s question stung a bit and Matthew’s look said so.

“Oh. I didn’t mean that the way it sounded.”

Simon and Matthew were unlikely friends. And it had been pretty rocky between them at first.

Simon had been a zealot with a lethal hatred of the Romans. He had once sworn himself to the sacred cause of driving them out of Israel. But even more he had loathed Jews who were complicit in the Roman subjugation and pillaging of God’s people. Jews like Matthew.
Matthew had collected taxes for Rome — and himself. He had simply seen it as a shrewd and lucrative career move. And prior to Jesus calling him from his booth he had had zero time for the foolish zealot idealism of people like Simon. Theirs was a utopic delusion — a handful of angry Jews taking on Caesar’s legions. It was a death wish, an appointment with a Roman cross.

Now they, the former zealot and former tax collector, were friends. Only Jesus could have made that happen.

“What did you mean?” Matthew asked.

“I just meant . . . you used to be . . .

“A shrewd dishonest manager?”

“I’m not saying you were just like . . .”

“Stop tripping over yourself, Simon. I was every bit as shrewdly dishonest and worse. I know it. It’s just painful to remember what I used to be.

“Which master are you saying commended the manager?”

“Well, that’s where I’m confused. It almost sounded like Jesus commended the self-protective actions of the manager. But I know that’s not right. How is this corrupt scoundrel supposed to be an example for ‘the sons of light’?”

Matthew smiled and replied, “Generosity.”

“Generosity? The only thing he was generous with was his master’s money!”

“Exactly. Simon, that’s our Master’s point. The manager used his master’s money to win favor with those who could provide him a place to live when he lost his job.”

“And that’s a good thing?”

“No. But as a ‘son of this world’ he knew how this world works. So he used worldly shrewdness so he wouldn’t be homeless. Even his worldly master appreciated his cunning. Jesus is saying that the ‘sons of light’ need to be at least as shrewd about how the kingdom works.”

Simon replied, “Which is completely different.”

“Completely. But what we do is similar to what the dishonest manager did.”

“You mean we’re generous with our Master’s money.”

“Right.”

Simon thought for a moment. “So, it’s just what he meant by “sell your possessions, and give to the needy” so that we will have “a treasure in the heavens that does not fail” (Luke 12:33). Shrewd ‘sons of light’ give away “unrighteous wealth” and make friends of God, who is our eternal dwelling (Deuteronomy 33:27).

“Exactly. That’s the shrewdness our Master commends.”

________

Our heavenly Master has made us all managers of “unrighteous wealth” (Luke 16:9). As John Piper says,

The possession of money in this world is a test run for eternity. Can you pass the test of faithfulness with your money? Do you use it as a means of proving the worth of God and the joy you have in supporting his cause? Or does the way you use it prove that what you really enjoy is things, not God?

These are questions we all must ask ourselves. Because Jesus wants us to be shrewd with our money (Luke 16:8–9), and kingdom shrewdness looks like this:

Fear not, little flock, for it is your Father's good pleasure to give you the kingdom. Sell your possessions, and give to the needy. Provide yourselves with moneybags that do not grow old, with a treasure in the heavens that does not fail, where no thief approaches and no moth destroys. For where your treasure is, there will your heart be also” (Luke 12:32–34).